Betty Pearl's Sissy Stories 20.1
Sissy Story Archives (older stories) => Pre-2011 Sissy Stories => Topic started by: DaraJaney on April 28, 2008, 03:32:36 PM
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Frank and his mother went to stay with friends of the family for a few weeks of the summer. The Edgars were quite wealthy and had a big place on the outskirts of a country town. The main attraction for Frank was Lisa Edgar. She was a couple of years older than him at sixteen. He was quite besotted with her. She had gorgeous wavey blond hair and was quite well developed up front which made a big impression on him at his age.
On the first night he could hardly sleep for his thoughts of kissing her and being with her. He couldn’t think of anything that would give him more pleasure.
The next morning he was disappointed to learn that Lisa had been up early and went out. After breakfast his mother and Mrs Edgar went off to the shops. Frank had another interest which he wanted to pursue while the house was empty. He had developed a bit of a fascination with girls’ clothes. Since he’d reached puberty he found that, not only did the sight of a girl in a short pleated skirt turn him on, but the thought of wearing one also had an effect. Not having a sister, he had little access to girls’ clothes for any further experimentation.
He didn’t understand it and was quite confused by it but the urge was great. He sneaked into Lisa’s room. He opened a drawer and saw an array of panties and stockings. He could feel himself stiffening down below. He pushed the drawer shut. On the one hand the idea of wearing girly underwear was humiliating – if anyone ever saw him! On the other hand he was dying to know what it felt like.
He walked over to the wardrobe and opened it. Lisa wore mostly jeans and t-shirts but there were a couple of blouses and skirts. He saw a lovely pleated skirt. He took the hangar out and admired it.
Just then the door opened and Lisa walked in. “What the ….?” Frank initially froze but then quickly placed the hangar back. Lisa smiled. “Hello. What’s all this then?” He went beetroot. “I’m sorry. I was just curious … Sorry.” He hung his head in shame. Caught going through her things.
Lisa went over to the wardrobe. She was still smiling. She took out the pleated skirt and looked at him curiously. “Would you like to wear it then?” Frank felt sick at the idea of someone knowing his secret. He tried to laugh it off. “Don’t be silly!”
She waved the skirt about and ran her fingers through the pleats. “Sure?” Frank dearly wanted to wear it but couldn’t admit it. “Yes I’m sure!”
She looked at the front of his trousers. “What’s this then?” Frank looked down. He had an obvious erection. He desperately tried to cover it with his hands. “It’s OK. I don’t mind”, she tried to reassure him. Again he denied it nervously. “I think you’d look cute”, she told him. He gulped. Would he ever get a chance like this again? But would she tell anyone?
“Come on, it’ll be our secret”, she said as she realised that he definitely wanted to wear the skirt. She reached towards his belt buckle. Now he was really confused. The girl he was obsessed with wanted to undo his trousers. But it was to put him in a skirt.
She coaxed him out of his trousers. He stepped into the skirt. She pulled it up around his waist and pulled up the zip. He couldn’t believe that he was actually wearing a pleated skirt.
She moved him in front of the mirror. He looked at himself nervously. It looked fantastic. He loved the feel of the air circulating under the skirt and around his bottom. He moved a little and was thrilled as the pleats rippled.
But he now had the hardest erection. He was wearing boxers which did little to contain it and Lisa giggled at the obvious point made in the front of his skirt. She went to the chest of drawers. She took out a pair of white panties. “These would be better”, she told him. If it was possible, his erection grew even bigger.
He wanted to deny that he had any interest in wearing her panties but he was actually speechless. His member was completely betraying him. There seemed little point in denying it. She handed the panties to him. There was a thin lace trim around the legs.
He had to be really careful removing his boxers. The slightest wrong move would set him off and he didn’t want that to happen in front of her. He pulled the panties up and stretched them over his erection. At least they kept his member pressed against him.
Now as he walked the tight panties stretched a little and he almost exploded. He had to stop and try to think of something else for a minute while his excitement eased. Lisa fetched a lovely white blouse. She helped him take his t-shirt off. He took the blouse. “Just a minute”, she said.
She opened another drawer and took out a white bra. She dangled it in front of him with a quizzical look on her face. He couldn’t take his eyes of it which answered her question. She pulled it over his arms and hooked it up at the back. She fetched some tissues and stuffed it for him.
He pulled on the blouse and she buttoned it up over his false bosom. She was clearly enjoying this and he was going weak at the knees.
She went to the drawers again. She took out a pair of rolled up white socks. When she unfurled them he could see that they were thigh-highs with a pink bow at the top. That very nearly did it. His heart skipped a little.
He was completely unable to resist now and within a minute he was standing in front of the mirror adjusting the bows on his stockings that came to just below his pleated skirt. Lisa produced a pair of t-bar shoes with a two-inch heel and strapped him into them. He walked back and forth absolutely thrilled at the girlish walk the shoes forced on him.
Lisa wanted to put some make-up on him. He was completely in her thrall now. She powdered his cheeks a little. She made him pursue his lips as she applied a little lipstick. She got a scarf and tied it in his hair.
He stood looking at the mirror in disbelief. He had wondered about these feelings for so long – what it was like to wear girls’ clothes – and all of a sudden here he was, wearing a short pleated skirt, blouse, bra and panties, pretty thigh high stockings and high heeled shoes.
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“Have you ever worn suspenders?” she asked him. Again he was speechless at the prospect. He was aware of stockings and suspenders from TV and movies but he had never actually seen a woman wearing them in the flesh as it were.
He took off the t-bar shoes and thigh-high stockings while Lisa went looking for a pair of black stockings and suspenders. She brought them over to him and a shiver of anticipation went down his spine. She lifted his skirt and put the suspender belt around his waist and clipped it in place. She rolled up a black stocking. His heart went all aflutter.
He held out his right foot as Lisa rolled the stocking over his foot and up his leg. She took a suspender strap and showed him how to attach it to the stocking. She told him to do the other strap himself. He twisted to reach it at the back. He stretched the stocking and the strap towards each other. The strap snapped back. Lisa tittered. “Keep trying. You’ll get it eventually.”
He got it at the second attempt. She helped him roll up the other stocking and he did up the suspenders. She signalled him to come over in front of the mirror. He started walking and stopped suddenly as he felt the stockings and suspenders stretch and slacken as he walked. He squeezed his eyes shut. He was so aroused he was sure to come. He thought about trousers for a moment and it passed.
He was completely taken with the stockings and suspenders. He could feel them move with every single step. He turned to walk across the room the other way. Lisa put her hand to her mouth to stifle a snigger. He hadn’t noticed the seams down the back of his stockings.
She fetched a pair of three-inch heels and put them on him. He tottered a little at first and had to steady himself. In front of the mirror he pulled up the hem of his skirt to see the stocking tops and the suspenders. He could also see the firm bulge under the panties.
“Why don’t we take a little walk outside”, Lisa suggested, guessing correctly that that would send another frisson through his body. But he was nervous. “Oh! I don’t think I should.” “It’s OK the garden isn’t overlooked.”
She took him out the back door. He hesitated for a moment before taking a careful step out the door. The wind rippled his pleated skirt and he could feel its cooling effect between the tops of his stockings and his panties. It was so thrilling.
He walked back and forth while Lisa looked on amusedly. She went for the side gate. “Why don’t we just go a little further?” Frank looked at her nervously. The thought of going out in public like this gave him quite a thrill. But he would be so humiliated if anyone realised that he was a boy. He couldn’t decide.
Lisa opened the side gate. He realised that she had closed the back door of the house and he didn’t have the key to get back in. “Or you can wait here until our mothers get home”, she teased.
It was enough to tilt the balance in his mind. He tentatively moved towards the side gate. He tugged the hem of his short pleated skirt. He felt that delightful tug of the stockings. He was in heaven. But he was still terrified of being found out.
He was practically shaking as they went out onto the footpath. He looked up and down nervously. There was nobody about. They walked towards the main road. There would definitely be lots of people around there. Still, he could just walk towards it a bit.
Then a woman appeared out of a gate ahead of them. She saw them coming. Frank stopped suddenly. He couldn’t bring himself to walk towards this stranger dressed as he was in a short pleated skirt, white blouse, stockings and suspenders and high heels.
“Don’t stop now or she’ll be suspicious”, Lisa whispered. Frank pulled himself together and tried to look confident.
“Hello Lisa. Who is this?” the lady asked. “Hello Mrs. Wise. This is my cousin Frances. She’s from out of town. Mrs. Wise looked Frank up and down. She didn’t seem to approve of the short skirt. “Well hello. You’ll be a big hit with the boys around here.” Frank frowned at that thought.
Lisa continued on towards the main road. Frank had no choice but to follow. Soon he was walking past several people and cars were whizzing up and down. A gust fluttered his skirt. He tried to hold it down. A passing man was clearly amused.
Frank found it difficult to keep up with Lisa in his high heels. They forced him to take dainty little steps and he had to scamper along occasionally to keep up.
Soon they were approaching the shops. Frank couldn’t believe he was doing this but Lisa just strode along not leaving him much choice. When she got to the coffee shop, she pushed open the door. Frank stopped suddenly. Surely she wasn’t serious. There were dozens of people in the shop.
She held the door open for him. A few people inside turned to see what was up. He knew if he caused a scene it would attract more attention. He walked in giving Lisa a cross look.
Once inside she made a bee-line for a booth in the corner. “Hi Carla. Hi Isobel.” “Hi Lisa” they replied. They looked at the curious girl behind Lisa. Frank practically cringed but had to stop himself.
“This is Frances, my cousin.” “Hi!” The girls smiled but in an obviously forced way. They looked Frank up and down.
Lisa slid into the booth. Frank followed her quickly, anxious to get his legs under the table. He shivered a little as the cold leather chilled the tops of his legs. The skirt was too short to go under him when he sat.
Lisa chatted away as if everything was normal. Frank smiled and tried to act like a normal girl but the others were clearly a bit puzzled. He was too nervous to say much.
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They had tea and biscuits but he was dying to get out of there. He was so relieved when Lisa said that they had better be off. He slid out of the booth and stood up. He tugged at the back of his skirt to make sure it wasn’t sticking up.
The stockings felt like they were being stretched tighter than before. They seemed to have slipped down a little while he sat. He was very anxious that the tops of his stockings might be showing.
“I just need to powder my nose”, he squeaked. Lisa followed him in. He went to the mirrors in the loo and checked on his stockings. Sure enough, he could see the dark black band at the top of his stockings. He reached under his skirt and pulled the stockings up further.
“Here, let me show you”, Lisa said. She demonstrated how to shorten the strap on the suspenders. Frank repeated this on the other three. When he was done he turned his back on the mirror and twisted to see how he looked from behind. “What the…” He saw the seams. Lisa tittered. He glared at her. “Come on, we better get going.”
They headed back to the house. Frank got a wolf whistle from a building site and Lisa was highly amused. When they got back to the house her mother’s car was there. Frank froze. “Damn! How am I going to get in without them seeing me?”
Lisa turned and looked him up and down again. “Well, come on in and let them see you.” “You gotta be kidding”, he gasped. “I’m sure your mother will be very understanding”, she assured him. “You really shouldn’t keep secrets like this from her.”
Frank was not so sure. Just then his mother appeared at a window. She stopped and looked out at Lisa and the strange girl with her. Frank realised that his mind had been made up for him.
They walked towards the front door. Frank was in danger of wetting himself. His erection was well and truly gone. He’d carefully kept this secret from his Mum and now she was going to find out.
They went in. The two mothers looked at Frank not entirely sure what they were seeing. Lisa decided to explain. “I found out that Frank likes to wear girls’ clothes.” Frank cringed. The two women’s jaws dropped simultaneously.
Frank shifted from one high heel to the other. They hurt quite a bit but that wasn’t the main thing concerning him at that moment.
His mother came forward and took him by the arm. “Oh honey, why didn’t you tell me?” Frank felt like crying. “It’s… kind… of… hard…. to” he sniffed. His mother smiled at him. “That’s ok honey.” Then she perked up. “You look really cute!” Frank was taken a-back. He sniffed again. “Really?” Lisa’s mother obviously decided to be supportive too. “Gorgeous, dear.” She sat down beside him.
Frank was so relieved but still a little ashamed at his revelation. Within minutes the women had decided to continue as if everything was normal and Frank sat there still in his pleated skirt and stockings and there didn’t seem to be any need to take them off.
Over dinner the women chatted about what other outfits he would look good in. He was quite embarrassed but yet again the thought of trying out other outfits was very tempting.
When it came to bedtime he went up to his room. Lisa came in with a pink see-through nightie. “Would you like this love?” His eyes stood out on stalks. He didn’t need to answer.
She showed him how to remove his make-up and gave him a peck on the cheek before she left the room. “Sweet dreams.” The whole day had been like a dream for Frank. He was still nervous about so many people suddenly knowing his secret but he was thrilled, none the less, that he had finally got to wear so many clothes that he had wanted to for so long.
When he was alone he sat on the side of the bed and sighed heavily. He was suffering a serious groin strain from being continuously aroused all day. He grabbed a handful of tissues. He had to be very, very gentle but he had no difficulty bringing himself to a climax with all the thoughts of the day swirling in his head.
The next morning Lisa woke him. “Rise and shine!” She pulled back his bed clothes and smiled at the sight of his nightie. She grabbed his arm. “Wait until you see this.”
They went up the stairs to the attic rooms. These probably used to be servants’ rooms in the old days. There were a couple of trunks in the corner. Lisa opened one of them. Frank’s jaw dropped open. There were several girls’ party dresses in the trunk. Lisa took them out one by one.
Frank’s mind was swirling with the thoughts of wearing one of these dresses. They were so sissy, but he would give anything to know what it felt like to wear one. Lisa held up a yellow cotton eyelet dress. She looked at him. She didn’t have to ask.
There was a full length mirror in the room. She manoeuvred him in front of it. He looked at himself in the yellow party dress. He was wearing white tights with lace-trimmed ankle socks pulled up over them and the t-bar shoes. He couldn’t see them, but he was wearing matching yellow eyelet panties pulled up over the tights. Lisa tugged the white sash tight and tied it in a bow at his back. The ends of the sash draped beyond the hem of his dress. She took a huge yellow bow and clipped it to his hair.
He was transfixed by his own image. Once again, it showed only too well just how much he loved the clothes. Lisa put her hand to her face to suppress a laugh. “You really are terrible.” Frank clasped his hands in front of his embarrassment.
“I know!” she exclaimed and she went to the other trunk. She produced a voluminous petticoat. Frank almost salivated. One didn’t see these often now but on the rare occasions that he did, he realised that there was nothing in the world he wanted more.
She pulled the layers of petticoats up under his dress. It did the trick of hiding his erection even though it could only have made it even bigger. He noticed that the petticoats had the effect of making the dress shorter on him.
Lisa stood back and admired him from behind. “I love those lacey socks.” Frank couldn’t see them because of the huge petticoats so he leaned forward for another look. Lisa burst out laughing. He straightened up quickly. It was obvious that his panties showed if he leaned over in the slightest. He was momentarily embarrassed but then looked at himself in the mirror again and just loved it.
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He couldn’t believe that here he was wearing a pretty party frock, tights, matching panties, layers and layers of petticoats and a huge bow in his hair.
“Wait until your Mum sees you!” Lisa pulled him by the hand. Frank wasn’t at all sure that he wanted his Mum to see him in such a sissy dress but Lisa was so excited it was hard to resist.
She brought him into the kitchen. There was an initial shock on the faces of both mothers but they were soon telling him how pretty he looked. They fussed over him and primped his petticoats and commented on the frilly socks.
Lisa’s Mum said “I do hope he’s wearing the matching frilly panties.” Frank squirmed and they all laughed.
They went to sit down to breakfast. Frank wasn’t sure what to do. “I’d better go and change out of this.” “Nonsense, honey”, his mother said. “You can wear whatever you like.” Frank smiled uncertainly.
“You have a whole three weeks to try out every frock in the house”, Mrs. Edgar told him. Frank was utterly thrilled at the prospect. But then he thought: did he really want to spend a whole three weeks in dresses?
He was very conscious of the feel of the petticoats and the tights. He could feel his highly aroused member pressing against the frilly panties. Oh what an opportunity!
He sat down to breakfast. The women watched as he tried to smooth all the petticoats under himself.
Afterwards he said to Lisa “I’m not really sure I should wear these all the time.” “Come with me”, Lisa instructed him. They went up to his room. She gathered the boy’s clothes that he had been wearing yesterday. She stuffed them into his suitcase along with his other clothes. She zipped up the suitcase and locked the zips together with the little padlock. She removed the key and put it in her pocket.
Frank squirmed and smiled shyly. He was simultaneously thrilled and appalled. But the decision had been made for him. He was going to spend the next three weeks in pretty frocks and frillies.
Much as he would love to spend all day in the party frock, even Frank knew that it wasn’t very practical. Lisa found a nice blue dress in the trunk which had a subtle thin lace trim around the hem and sleeves. Frank wore white knee-high socks with it and the t-bar shoes.
As he sat casually reading a magazine, he became quite thrilled at the thought of spending the three weeks in dresses. When Lisa suggested going into town, he got that little frisson again. He checked his dress in the mirror, pulled up his socks and was all set.
As they walked along the main street, he did attract a little attention. He guessed it was probably unusual nowadays even for a real girl of fourteen to wear a dress and knee-high socks. Girls around that age or even younger seemed to be particularly amused by his pretty clothes. But he was getting such a thrill he wasn’t going to let it bother him.
Once again Lisa met her friends, this time in the ice-cream parlour. The girls gave each other looks when they saw Lisa’s “cousin” in the goofy dress. Arlene told them her younger sister was having a birthday party the next day and she thought Frances might like to come. He wasn’t sure how genuinely this was meant.
Frank was a little unsure but Lisa more or less answered for him. “That’s great, isn’t it? Thanks for the invitation.”
Later Lisa said to him “now you have an occasion to wear one of those party dresses.” Frank wasn’t so sure. Girls probably didn’t wear stuff like that to parties anymore – not any girl over eight anyway. But the idea of wearing one of those dresses was hugely tempting.
The next day as Frank looked at himself in the mirror he was still torn over it. He just loved the pink dress with those three layers of flouncey lace. The petticoats were shot through with pink too. He was concerned about the pettipants though. They had an inch or two of leg and there was a big risk of them being seen which would be mortifying for him but they were just so gorgeous.
He wondered was the day too warm for thick white tights but he couldn’t help himself. He bent over and fluffed out the pink lace trim on his ankle socks. Then he straightened up quickly remembering the pettipants. He was going to have to be careful.
Lisa had shown him how to use the curling tongs and she had tied the curls up on either side of his head with pink ribbons. He tugged at the lace trim of his white gloves.
He had such a hard erection. He fluffed out his petticoats, concerned that even under those layers of organza he might be given away. He looked at himself again. An eight-year-old would be embarrassed by this outfit. He couldn’t do it.
He paced across the room. The petticoats tickled the tops of his legs and swayed around him as he walked. He turned quickly and his petticoats twirled around him. He just couldn’t help himself. He couldn’t bring himself to take this outfit off now.
Lisa took him by the arm and led him from the room. He couldn’t believe that he was really going to go out in public like this.
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Lisa knocked on the door of Arlene’s house. Frank squirmed in his pink party dress. He knew this was mad but he couldn’t help himself. He pressed his knees together and felt the friction of his tights. He pushed his petticoats down, growing increasingly concerned about his pettipants being seen. He knew the pink frilly lace on his ankle socks was too much really. He could feel an enormous erection beneath those layers of petticoats.
The door opened. It was too late to do anything now. He straightened up and tried to look confident in his party frock. Arlene’s mother smiled at Lisa and then her smile dropped momentarily when she saw what appeared to be a mid-teen age girl dressed like a very sissy eight-year-old. She recomposed herself. “Well hello, this must be Frances. What a pretty dress.” Frank blushed. He probably would have instinctively curtseyed if he was sure how.
“Ehm, we didn’t really expect people to dress up for the party”, the lady said, trying to warn Frank that he might be a tad out of place. She stood back from the door. Half-a-dozen teenage girls were standing around the lounge. Frank searched for one wearing a dress or skirt of any kind. They all wore jeans and t-shirts. This was going to be worse than he thought.
He stepped in uncertainly. What had he let himself in for? He was hugely conscious of the petticoats swishing around him so he tried to hold them down. That made him remember his white gloves. He could see the girls taking in every detail of his outfit. The lacey socks, the white tights, the flouncey petticoats. They were clearly trying not to laugh. Frank was mortified. His pen-is stretched against his pettipants.
Arlene’s sister appeared, and being rather hyper on her birthday was less inclined to hide her amusement. “Hi …ehm … Frances. Glad you could come.” Frank sensed that she was delighted to have this unexpected added spectacle at her party.
Frank was invited to sit and asked if he would like a drink. They all watched eagerly as he fussed with his petticoats before sitting. Even when he sat down his dress didn’t reach his knees and he was very concerned that anyone sitting opposite might see his pink pettipants. He clamped his knees together and pushed his petticoats down either side as best he could.
One of the girls went out into the garden. He could hear excited whispering and over the next few minutes other girls came in, obviously tipped off about the really sissy girl who had just arrived.
After a short while, Arlene’s mother announced that they were taking a trip to the adventure centre in the town park. The mothers were going to drive them all down in their cars.
Frank ended up in Mrs. Edgar’s car. He sat in the centre of the back seat. He had to gather his petticoats in so that Lisa could squeeze in on one side and Arlene on the other. It ended up with Frank’s head sticking up out of a mass of petticoats all squished up around him.
When they got to the park he had quite a job trying to restore his petticoats to some kind of order. As he shook them and smoothed them Arlene thought she caught a glimpse of pink frilly panties but she wasn’t sure.
The other children all ran towards the climbing frames and swings and roundabouts and rope bridges. Frank knew that there was nothing he could do but watch. There was no way he could attempt to go on any of the apparatus in his short and flouncey dress. His petticoats would be sure to get caught on something or his tights would snag. He would definitely end up exposing his frilly underwear and he wanted that least of all.
He felt so dumb sitting demurely on a bench with his petticoats arranged around him watching all the other kids have so much fun. Arlene’s mother told him she was heading back to the house a little early to set up the birthday cake. She asked did he want to come with her since he couldn’t do much at the park. He accepted the offer happily. Arlene’s little brother and his friend came too, since they were happy to get aware from the girls.
When they got back to the house Frank offered to help. “Thanks but I have it under control. Go on out into the garden.” Arlene’s brother grabbed Frank’s hand. “Come on we’re playing cowboys and Indians.”
Lisa arrived back just ahead of the posse. “Where’s Frank…ces” she asked, correcting herself at the last minute. That was close. “Out in the garden playing with the boys.” Lisa looked out the kitchen window. She put her hand to her face and ran out into the garden.
Frank was tied to a tree and had a gag stuffed in his mouth. The boys ran off when they saw Lisa emerge. They had tied Frank’s petticoats up around his arms and the full extent of his pink frilly pettipants were exposed for all to see.
Lisa ran across. About a dozen girls appeared out into the garden. Frank tried to turn away from the house as far as the rope would let him. This wasn’t doing anything to conceal his pettipants. But when Lisa reached him she saw the enormous erection underneath. If anyone saw him up close it would be immediately obvious that he was a boy in a sissy party frock and frilly panties – and clearly thrilled by it.
Lisa quickly untied the knot and helped him lower his petticoats just in time as the gang of girls approached. Frank was sniffling. Arlene’s mother had seen what happened. “I’ll kill those boys!” But Frank could see she was amused by his display of underwear.
Lisa brought Frank home. He figured himself that this humiliating experience would put an end to his desire to dress up in frilly clothes. But when he caught himself in the mirror again he still felt that frisson and another erection appeared.
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So he continued wearing dresses and skirts for the rest of the three weeks. Every night he would grab a box of tissues and relieve the erection that had been there the whole day.
As the end approached, he started to grow sad. Detecting this, Mrs. Edgar told him “you can stay with us for the whole summer if you like.” As usual Frank was torn. The idea of another five or six weeks in nothing but dresses was thrilling but he still felt guilty for wanting it.
But would he ever get a chance like this again? He was able to wear whatever pretty, frilly, girly clothes he wanted. He continued to be embarrassed by the funny looks he got in public but just couldn’t help himself. He had no interest in wearing sensible pencil skirts or ordinary t-shirts. What was the point in being a girl if you couldn’t wear the prettiest dresses?
He opted to stay and his mother was happy enough with that. If her plan was to hope that he would grow tired of it, it didn’t work. Every day he still thrilled at the feel of tights and petticoats or at the thought of the lacey underwear that lay beneath.
With a week to go he was starting to get that sad feeling again. Mrs. Edgar sat him down one day. “I’ve spoken with Sister Brigid at the convent. They’ll take you in to the school if you like.” Frank was taken by surprise. A chance to continue wearing dresses. But if he did this, would he have to finish his four years of school as a girl?
He still had confusing feelings. He was a boy. He didn’t actually want to be a girl. He just wanted to be able to wear pretty frilly dresses. It wasn’t the same thing. But to go to school every day would mean that he would have to act convincingly as a girl - perhaps for years.
But there was probably no other way he could continue to wear dresses and skirts. If he refused, next week he would be back at home in the boring grey trousers of his school uniform. “You’d have to wear the uniform”, Mrs. Edgar said with a little smile. He was definitely interested. “It’s a blue plaid pleated skirt.”
On the first day of school, he examined himself in the mirror. He straightened the knot in his tie and tugged at the collar of his crisp blouse. One of the pleats in his skirt was kinked so he smoothed it out. The skirt fell a few inches short of his knees. He took care to wear simple blue panties – there were boys at this school too. He pulled up his white knee-high socks and checked that his t-bar shoes weren’t scuffed. Finally he tugged the lapels of his light and dark blue striped blazer. He loved this uniform. His pig tails poked out either side of his head with blue ribbons tied in bows.
His mother looked at him proudly as he stood to go out the door. His uniform was perfect but she fiddled with it anyway and sent him off.
He marched down the road looking down at how his skirt rippled beautifully. He turned onto the main road. Some girls appeared on the other side. He frowned at the state of their uniforms. Their skirts came almost to their ankles. Their off-white socks sagged. Their blouses were often not tucked in and their ties were very loosely tied – if tied was the right word at all.
Others joined them on the way. None of the girls wore the smart blazer but shabby cardigans and sweaters instead. He could see them look out the sides of their eyes and snigger at his prim and proper uniform.
He tried not to let it bother him and he continued towards the school. In the school yard he was the centre of attention. “Look at Pippy Longstocking”, someone sneered. He was relieved when teachers appeared and the teasing stopped.
He continued to get stick because of his oh-so-perfect uniform. But wasn’t going to give in to them. He wasn’t interested in going to school as a girl unless he could wear a smart pleated skirt and snow white socks. He wondered just how strongly he was committed to spending the whole year as a girl.
He became quite unhappy. He wanted so much to wear pretty dresses and skirts but, other than Lisa, her mother and his own mother, everyone else teased him and made fun of him. He complained about the continuing hard time he was getting at school.
One Saturday he was rummaging again in the trunks. Right down at the bottom he found some patterns for dresses. They seemed to be even more sissy than his party frocks. Then he realised that they were baby dresses. Just then Lisa came in. “What’s that?” She went over to him and took the magazine. “Oh my! Does Francie want to be a little baby girl?” “No, don’t be silly!” “You mean you wouldn’t like to wear one of these really pretty dresses?” He put his hands on his lap trying to hide the answer. But Lisa knew him well enough.
She laughed it off and left the room. He couldn’t help wondering afterwards though what it would be like to wear such babyish dresses.
That afternoon Lisa called him into the lounge. She had some shopping bags. “Look what I’ve rented for you.” She produced a big pink baby dress, flared at breast level and covered with layers of lace. It was obviously an exaggerated fancy dress costume. But he couldn’t take his eyes off it.
He was so embarrassed at the thought of wearing a baby dress that Lisa had to cajole him for ages. But she knew he wanted to.
Eventually she was buttoning up the back of the dress on him. She took him to a mirror. It was really really short on him. It barely covered his panties. She produced a matching bonnet and placed it on his head, tying it under his chin in a bow. Then she popped a big pink soother into his mouth. She stood back and looked at him and smiled.
He was so thrilled. He knew he must look so ridiculous but it felt great. He had such an erection. Lisa called their mothers. He cringed but they appeared almost immediately. “Look at our pretty baby girl”, his mother said. Frank went beetroot. He suc-ked on his soother to complete the effect.
“There’s one more piece”, Lisa remembered. She took out a pair of huge matching panties. She pulled them up over the panties he was already wearing. The thick lace of the baby panties could be seen below the hem of his dress.
-
The women ooh’d and aah’d. “But it’s not quite right”, Mrs. Edgar said. She disappeared. Frank could hear all sorts of rummaging noises upstairs. Then she reappeared.
She had two triangular white towels and something that looked like a shower cap. When Frank saw the big pink pins he realised what she was at. “Oh … no … I don’t think so.” But the women knew better than to believe him.
Minutes later he was pinned into a nappy. The “shower cap” turned out to have leg holes and was pulled up over his nappy. His mother removed his knee-high socks and replaced them with thick white tights. Then they pulled the baby panties up and they fitted quite snugly over his thick nappy. “Perfect!” his mother said.
Frank had such a hard erection smothered in the nappy. This was incredible. The women wanted to treat him just like a baby so he found himself suc-king on a baby bottle of milk.
Before long Lisa produced a play-pen and they made him sit in it. He was half mortified but really loving it. They found lots of baby toys and spent an hour or two playing with him.
But all good things come to an end, he thought. He removed the soother. “OK Mum. I need to go to the toilet.” He stood up. “So?” his mother asked, holding the side of the pen where he wanted to get out.
He looked at her. “Go on then”, she said nodding down at his nappy. He was shocked. “It’s a real nappy. You can go in it if you like.” Frank immediately felt another erection. His mother smiled at his hesitation. It was already decided. He sat down in the pen again. She popped his soother back in.
He could hardly move with anticipation. What would it be like to wet his nappy? He had such an erection there was no way he could pee. The women tried to busy themselves but he knew they were just dying for him to tell them his nappy was wet. He had to concentrate on playing with the letter blocks until his erection died down. Then he let go. This amazing warmth spread right around his nappy.
He felt so humiliated and exhilarated at the same time. He was going to have to tell his mummy that his nappy was wet. “Mmmpppfff” he called to her through his soother. “Yes honey?” she asked in studied ignorance. “Is your nappy wet dear?” Lisa and her mother gathered round. He hesitated. Then he nodded. They were clearly delighted but tried to play it cool.
They let him out of the pen and brought him to the back room. A table had been set up to change him on. They made him lie back on it. Lisa pulled his dress up around him. He desperately wanted to see everything but couldn’t see past his dress. So he had to experience this entirely by the feelings.
His mother pulled down his panties, then his tights. She then carefully peeled off his plastic panties. Then he felt the soggy nappy loosen as she undid the pins. Then she was wiping him. She told him to turn over. She wiped his bottom and then he felt powder being sprinkled on him.
He turned back and she further powdered his front. Then she pointedly held up a clean nappy. “Now we have a nice clean nappy for babykins”, she told him. He didn’t object. Soon he was sitting back in his pen in a clean nappy with his tights and panties restored.
When it came to dinner time they pureed his dinner in a food-processor and spoon fed it to him. They gave him another bottle.
At eight o’clock they wanted to put him to bed. He didn’t like this bit. “Now if you’re going to be our babykins you have to be a proper baby and get your beauty sleep.” He still didn’t like it but he was enjoying the whole experience so much, he went along with it.
They tucked him in, still in his nappy. He lay there stunned by the day he just had. He wasn’t the least bit tired. So he thought again about the experiences of the day and managed to come in his nappy. He heard the others going to bed much later before he nodded off.
He woke at about 4am dying to go to the toilet. He wondered should he go in the nappy. Well, they wanted him to be a real baby so ….
He wet himself and lay back wondering if he should wake his mother. His nappy started going cold which made his mind up for him.
She wasn’t at all happy about being woken but went through the motions of changing his nappy and pinning him into a clean one.
The next morning Lisa spoon-fed him his corn flakes. Later on he felt the need to do a number 2. He gurgled through his soother. “What is it dear?” He removed the soother. “I need to do a number 2”, he said shyly. He was pretty sure that they wouldn’t want him to do that in his nappy. His mother thought about it. She shrugged. “Go ahead.”
Once again Frank was in emotional turmoil as he faced the prospect of soiling his nappy. It was going to be such a mess. But he wanted to know what it felt like. He got up on his knees. He pushed until he felt a plop in his nappy. He couldn’t believe what he had just done.
-
They seemed happy to continue treating him like a baby all through Sunday so he played along. When it came to bedtime his mother said “I don’t want him waking me in the night to be changed, though.” Lisa was just feeding him the last of a baby bottle of milk so it seemed certain that he was going to wet himself during the night.
“Just a minute”, her mother said. She reappeared carrying what looked like a much thicker nappy. It was also square. She laid it out in a diamond shape on the changing table and pulled the sides in from the points. Then she told Frank to get up on the table.
“Now if you fold this point up a few times it makes for a really thick front on the nappy for very good soakage”, she explained as she folded it up between his legs. She pinned the thick roll to the part that went around his waist. When she was done he found that he couldn’t close his legs much. She pulled a much bigger pair of plastic pants over his nappy and tucked everything in.
He lay back in the bed. The nappy was so thick around him. “Now you’re not to wake anyone for a change during the night. If you wet yourself, that nappy will take it.” He frowned at the thought but nodded.
He did indeed wet himself during the night. He just lay there. It went a little cold but it wasn’t as bad as the night before. Soon he went off to sleep again.
His mother woke him. “Did you wet yourself?” she asked as she pushed his soother in. He nodded. She ran her finger under the elastic of his plastic panties. “Not bad”, she concluded.
“You know”, she said softly, “if you’re really miserable at school, you don’t have to go today.” He looked up at her hopefully. He really was unhappy at school. But if he stayed at home did he have to stay as a baby?
“Do you want to go?” Put like that of course he shook his head. “Ok honey”, she kissed him on the forehead.
Frank wasn’t too pleased when she dressed him in his baby dress, tights and panties without changing him but he was becoming accustomed to not having a choice over these matters.
She led him into the kitchen and told the others that he wasn’t going to school. They were quite pleased for him. His mother continued to bottle and spoon feed him, changed his nappy after another wetting and put him in another towelling square. These thicker nappies really made him waddle.
Lisa’s mother arrived during the day with another baby outfit from the fancy dress place. This one was peach and had several layers of petticoats attached. Frank looked at it and felt that tightening feeling even in his thick nappy.
The next morning he wondered if his mother was going to make him go to school. In the event, she never raised the subject. She gave him a baby bottle of milk. But then she wanted to spoon-feed him some muesli. He hated the stuff and tried to push her hand away.
“Now honey, this is much better for you.” He shook his head firmly. “You need the roughage she insisted.” She forced a spoonful into his mouth. He swallowed and shuddered. He pouted but she insisted on continuing.
Lisa’s mother watched with interest. She popped out of the house for a moment. She returned with a packet of rusks. “Would you prefer these?” Frank looked crossly at her. He wanted his corn flakes. His mother poured milk over the rusks and half-mashed them. He let her put one spoonful in. It was pretty disgusting but at least it didn’t have that sawdust texture like the muesli. Grudgingly, he let his mother feed him the bowl of rusks.
Later that day when she was changing him she shaved all around his groin. He was curious but just suc-ked on his soother wondering what that was for.
When he was back in a clean nappy Lisa’s mother came back from the shops. “I was down at the hyper-market”, she said. “Some great bargains there, you know.” She went out to the car and returned carrying a large box. It was a wholesale carton of rusks. “40 packets” it said in the side. His mother was quite pleased. “That should keep him going for months.” Frank looked up in shock. Months? He looked at the huge box and thought about being kept in nappies and baby dresses for months. Or go back to school? He really hated these dilemmas.
The next day Lisa’s mother came in while he was playing in the pen. “I have a surprise for you.” He looked up with interest. She took from behind her back the book of baby dress patterns that had given rise to this whole episode.
“Do you see this?” she asked, pointing to a lemon baby dress with a white pinafore with huge wings over the shoulders. Frank gazed at it. “Ta-da!” She took out a Frank-sized version of the dress. The soother dropped out of his mouth.
She soon had him zipped into his new baby dress. He looked down at the lace-trimmed pinafore. He could feel layers of netting under his dress. Lisa tied a matching bonnet under his chin. His mother took a pair of powder yellow tights from the bag. His member was now at full stretch.
His mother made him step into the matching bloomers. He could feel the elasticated legs just above his knees. When they brought him to the mirror he could see that the dress only covered the top half of his nappy. The unmistakable bulge was obvious under his bloomers. Lisa turned him around. He looked over his shoulder. There were three lines of lace across his bottom and a big bow in the centre. He wanted to cry he loved the outfit so much.
-
But they weren’t finished. “And finally”, his mother announced. Frank was curious. This was all so fantastic what else could there be? She and Lisa pulled thick mittens over his hands and buckled them at his wrist. He examined them curiously. His fingers and thumbs were completely immobilised in the mittens. “To stop you getting into trouble.”
Lisa’s mother also had a carpenter hard at work. They brought him into the kitchen. In the middle stood a wooden high-chair. They sat him into it. It was equipped with a set of straps to hold him in and the tray had a special catch underneath that he couldn’t open with his hands in mittens.
He wriggled experimentally in the chair while his mother prepared a bottle. He spent several minutes squirming against the straps and tugging at his mittens but he was held tightly in the high-chair and his hands were completely useless. His mother smiled as she came over with his bottle. She removed his soother and pressed the bottle into his mouth. He was completely at her mercy.
After his bottle his mother smiled and said “now for your nap”. He gave her a puzzled look. This was new. She brought him into the back room. There was a large pink wooden cot in the corner. He froze. But his mother pushed him on.
She took off his bonnet, dress, bloomers and tights. Then she produced a pink sleeper. It was a thin flouncy dress with a short little flared skirt. She made him lie back in the cot. The dress had built in panties which she pulled under his bottom up his front. She pressed several fasteners together to hold this in place over his nappy. “There we are!”
She replaced the side bars. Frank was getting concerned. He got up on his knees and took out his soother. “How long are you going to keep me like this?” he asked cautiously. His mother pushed his soother back in. “Now, now. Real baby’s can’t talk.” “Mmmppppfff nnngggg ugghh eeennngg mmmyyy”, he protested.
“Well now, Lisa’s Mum has gone to all this trouble and expense honey.” Frank looked down at his new pink sleeper and then at the cot he was in. His mother took a pink leather harness. She pulled it over his arms. “You’re our little baby now.” She pushed his soother back in.
“Mmmppfff!” He tried to grab the bars of the cot but his mittens made even that impossible. His mother tightened the harness around him. This had been all very well as long as he was choosing what he did.
She attached the harness to a loop on the end of the cot. It gave him enough slack to move around the cot but he clearly would not be able to get out. He looked down again at the mittens that made his hands helpless.
“Sweet dreams love”, his mother said. “Mmmppfff” he replied and she left the room. He sat there wondering was she going to come back in a few minutes and explain that it was all a joke.
But she didn’t. He looked around the cot. The only thing there was a teddy. He examined the catch on the side of the cot. There was no way he could open it with his hands in mittens. He looked down at his harness and where it was attached to the cot. He had to accept that he was going to be in the cot until one of them decided to let him out. He didn’t like being at their mercy.
It was clear that if they had gone to the trouble of making him his own baby dresses and making him a high-chair and cot that this was not to be a short stint as a baby.
Eventually he lay down in the bed. There was nothing to do but clutch his teddy and suc-k on his soother.
Much as he was disturbed by his predicament, he was inevitably hugely aroused by it. He turned on his tummy and tried to rub his groin against the base of the bed to bring himself to climax. But in such a thick nappy, it made little impact on his member.
As he thought about being kept as a baby indefinitely his erection hardened. But he just couldn’t complete the job in such a thick nappy. He rubbed and rubbed himself but it was no use. He eventually had to give up and wait for things to subside. But he couldn’t take his mind off being a helpless baby in a pink dress and confined to a cot – since it was his actual situation. So the erection just kept returning. He suc-ked desperately on his soother hoping that that would relieve it.
It was at least an hour before Lisa came and let him out of the cot. “Now, off to your play-pen”, she told him. He waddled towards the door. “Don’t forget teddy”, she said. Frank turned to see that she was holding the strap of his harness. It was obvious he was going nowhere without the teddy. He went back and leant into the play pen, picking teddy up between his mittens.
He walked away and Lisa held his harness until he reached the play-pen. He had to wait for her to open the side before he could get in. She slipped the catch open and let him in. He flopped down in the centre and she locked it again. Then she tied the strap from his harness around one bar of the pen. She turned the TV on to the children’s programmes and left him watching Barney.
They got into a regular timetable of bottles and feedings and naps for Frank. For the first few days he didn’t sleep during his afternoon naps. He just writhed in the cot desperately trying to bring his erection to fruition.
But then he got into the habit of nodding off. Soon he came to associate his warm bottle of milk with the cosy feeling of being tucked into his cot with teddy under his arm. One day he woke to find his nappy wet. He didn’t know when he had wet himself but it must have happened in his sleep.
Mrs. Edgar wondered why he was crying when she went in to wake him. Since he wasn’t allowed speak he couldn’t explain. She stuck a finger in to test his nappy. It was damp but not in need of changing yet. She sniffed but there was nothing. She handed him his teddy. “There, there, did we have a bad dream?”
-
Another day he felt a little unwell before his nap. He drifted off anyway. After a while, he half woke. He could hear Mrs. Edgar. “I’m afraid a bad bang on the head did it.” He could just about make out a strange lady standing beside her with a clip-board. He desperately tried to wake up properly. He clutched his teddy tighter and suc-ked hard on his soother. “Ah the poor thing”, the woman said.
Then Frank realised that he had soiled himself badly. The stink was terrible. He shifted in the cot and realised that it was a terribly liquid poo. “Poor dear can’t help it”, Mrs. Edgar said.
“Mmmnnnnggg” Frank said. Unable to summon up enough co-ordination to even spit out his soother. “Fair enough”, the lady said, retreating from the smell. “I’ll come back in a month to see if there’s any improvement.”
Frank tried to sit up but the woman was leaving the room. “Mmmnnngggg” he protested as the strap prevented him from reaching the end corner of the cot.
Mrs. Edgar came back in. Frank gave a thoroughly puzzled look from his cot. “Sorry honey but we had to give you a little something to make it look convincing. Otherwise they might make you go back to school.”
Frank thought going back to school must be preferable to sitting in a cot in a dirty nappy. But he didn’t seem to have any say in it anymore.
A few days later he was sitting strapped into the high-chair being spoon-fed his boiled vegetables. Mrs Edgar told him “some of the other ladies on the street have heard about you”. Frank frowned. “It’s not possible to buy lots of rusks and bottles of nappy rash cream around here without someone noticing. I had to explain to them.”
Frank looked very troubled. Just what did she explain? “I explained to them that you are a fourteen-year-old boy who loves to wear frilly dresses.” His heart sank. “I told them how you ended up as our little baby”, she continued as she scooped up some dribbled parsnip from his chin.
“So there’s a few of them coming over this afternoon to see you!” she said brightly. “Mmmpppfff!” Frank complained. “It’s ok. They’re very understanding” she assured him. This didn’t make a bit of difference to Frank. He didn’t want these women seeing him in nappies and baby dresses. “Mmmnnnnggg!” “That’s right, it’ll be fun. There won’t be more than a dozen of them.” Frank slumped in the high-chair as she went to clean his bowl.
That afternoon he was strapped into his high-chair in pride of place in the middle of the lounge wearing his lemon baby dress, matching bonnet and bloomers, white tights, frilly ankle socks and with his hair freshly pressed into ringlets. Lisa added a little blush to his cheeks. She pressed a large doll under his arm. They stood back and admired him. He frowned from behind his soother.
The doorbell rang making him jump. He heard the chatter of women outside the door. He wriggled in the high-chair in one final vain attempt to escape. But then he wet himself as the chatter entered the hallway. That was his third wetting, he reckoned, and even his thick towelling square was going to feel uncomfortable now. But he didn’t think that this was the best time to ask to be changed.
The women were delighted to see the fourteen-year-old boy in a pretty baby dress. They chattered excitedly about his cute bloomers, pretty bonnet and white tights. They just loved his ringlets. Suddenly cameras started flashing. “Mmmpppfff!” This wasn’t part of the deal. Then Frank realised again that there was no deal here.
So now that it wasn’t a secret anymore and every Tam, Trish and Harriet seemed to feel free about dropping in. Four women were now making him new baby dresses from the patterns in the book.
Frank was now well used to his baby status. He waited patiently all the time to be let out of his high-chair, cot or play-pen. He suc-ked on his soother when he wasn’t being bottle or spoon-fed. He frequently found himself wet or soiled without remembering when he had done it.
On the anniversary of his first day in a skirt, his mother arranged a “birthday” party. He sat strapped into his high-chair in his brand new baby pink dress with the powder blue puffed sleeves and delicate taffeta pinafore. His pink frilly pantaloons were covered in rows of lace all the way down to his ankles. The six-inch brim on his bonnet meant he had to turn his head to be able to see anything outside the funnel view it accorded him.
About twenty women and former school-mates gathered round as the birthday cake was placed on the tray in front of him with one candle lit. His mother pulled the soother out of his mouth. He blew hard and the candle went out. His mother replaced the soother while everyone cheered.
A slice of the ice-cream cake was cut for him and Lisa proceeded to spoon-feed it to him. His mother opened all his presents for him which mostly consisted of dolls or rattles but included other bits and pieces. Someone bought him a new harness with “Baby Frank” written across the breast.
After all the guests were gone his mother spoon-fed him the last piece of cake. “All gone now”, she sang to him, “… until next year.” So not much sign of an end to this, he concluded.
[The End.]